Nilesh Ashra on the Expanding Intersection of Creativity & Technology

Mixing Board member Nilesh Ashra is an independent consultant and creative director who helps brands take a creative approach to emerging technologies. Before going out on his own, Nilesh was a Director of Creative Technology at Wieden+Kennedy, where he founded the Lodge at W+K.

In this Studio Session, Nilesh and Mixing Board founder Sean Garrett talk about what’s happening in machine-based creativity, why we can never stop learning (and why learning makes work more fun), and what HBO for the enterprise might look like.

SG: You have a very simple bio on your LinkedIn saying that you make things in the space between brands, humans, and computers — and then you try to make that feel fun and easy. I imagine making it feel fun and easy, that could be 20 years of work right there. Tell me more about that and how you ever even got to writing that sentence.

NA: That’s the question that’s probably at the root of how I’ve ended up in all of these strange and wonderful situations. When I was 11 years old, my uncle bought me a computer called the BBC Micro. It was one of those computers that had a green screen that came with a book called Programming for BBC Micro. He and I would sit up late into the night, punching out computer programs. The computer came with a book of programs, that’s how software was distributed. It was my first exposure to a type of creativity that resonated with me. I wasn’t a kid that wrote, drew, sketched or anything. I grew up in North London, in an immigrant family. My parents didn’t push us into the creative arts. But suddenly I could make this computer do anything. I started coding like a maniac, I just became obsessed with that creative act and that you can ask something of these machines.

Fast forward to college, I ended up doing a degree in AI, which is just a pointy ended, extreme version of computer science. I came out of college and completely accidentally fell into a job at a digital agency in East London. This was in the heyday of the internet, right after the first .com bubble burst, just as some of these companies were rising out of the ashes. I couldn’t believe that there were companies that were paid to make stuff on the internet for other companies.

There was something really chaotic and beautiful about that time of media. Every designer was also writing code. Every coder was encouraged to just like bang out a web design. We didn’t have account people. Everyone was just making stuff work.

That was the beginning of me realizing that code is a really creative medium. I lucked out because it turned out to be 1000% true. So many commercially viable and important creative acts from then until now have had a technology action at the core. Twenty years later and there’s no signs of slowing down. It actually feels like we’ve only just scratched the surface.

SG: How did you get to Wieden+Kennedy, this very famous, very big, very creative ad agency, notable for work with Nike and many others. If you’re in that world, it’s one of the pinnacles, if not the pinnacle. You showed up there on your first day, and what are you doing?

NA: Back then I hadn’t connected these dots, but 50–60 person agencies are basically three weeks away from going out of business in perpetuity. And then here’s Wieden+Kennedy. It’s like a temple that seems indestructible. Its reputation was insane. When I arrived, its roster of clients was insane — it was every single brand you’ve ever heard of, Nike was one of them. Everything about it, the building, the prestige, the people, the way that they spoke to each other about the work, was intimidating.

But I was brought there to do something, I was brought there as part of a mission to push the company outside of a specific type of executional craft. There was a backdrop of digital media, Twitter was blowing up, something was happening on social media — I was one of the few hires that was brought in to help accelerate their agenda. I was brought in along with a lot of senior people who were brought in from digital creative worlds, these true icons of digital tech. Many of those people didn’t last more than a year or two. It was like oil and water. Like chucking water into a hot deep fryer, it was explosive at times. If you want to talk about legacy and credentials, you can’t really play a game of politics when you have people that have that kind of legacy and credentials. When they fought the battle and things became political, a lot of that became really high friction.

I had a totally different approach. This is where I learned about making things easy and fun. I thought, wow, I got to move to America to this legendary company. Generally, people seemed more obsessed about ideas than anywhere I’d ever worked. But it quickly got really difficult to talk about those ideas when they weren’t in the TV advertising vertical. But if I could steer around that and just have philosophical conversations with people about — what is an idea and what does it mean to do something really big with this? How big could we make this? This is when you really start to speak the language of what Wieden+Kennedy’s DNA was all about. How do we turn this into an idea that every kid in America knows about? And can I help with that?

SG: I’m always interested in people who enter into these moments where things are converging. You have people who can ride the waves and people who get crushed in the undertow and pulled out to sea. How do you help people understand how to manage that and ride those waves? What about your own personal past allowed you to do this dual translation, to be a chameleon, and shift through conversations?

NA: I made a lot of mistakes and I learned from my mistakes there. A lot of how I navigated those early years at Wieden has become an operating system from which I now operate in my consultancy and in the products I’m creating. Fundamentally, it’s humility. And it’s not all altruistic, I’m not someone that sits on a cliff, meditating, looking at a sea with a total sense of calm. I don’t feel calm. My understanding of my own limitations comes a lot from fear. Fear that things are moving so fast. I’m not compelling you to explore this space because I’m sure that it’s the answer. I just know that we’re all going to wake up tomorrow and things are going to be even more different.

I don’t know what else to do other than just assume that we need to keep learning. We have to keep learning. If we don’t, the relevance of this entire company is going to be increasingly questioned, and that’s going to be bad for all of us. It’s not going to be something that impacts one department more than another. It’s going to mean that we’re going to have way less fun at work. Our job is world class, original thinking — in a really repeatable and high frequency way. If that’s our product, then we have to do this. It’s a necessity to actually understand that we have limitations today. And the only way to close that gap is through genuine curiosity and really deep learning.

SG: When you showed up there and you said, I’m going to do this job, Creative Technology, how did that definition change over the five years you were there? And how would you define it now?

NA: It’s always been a funny thing to define. We did it in phases. In the beginning it was a capability. It was something to bounce ideas off of — I have an idea, are there some experts that I can bring in to expand the conversation a bit? And then we swung into more than just an internal capability. We were on the front foot, we were exploring things proactively.

There were three or four areas that we were really convinced were going to be a very big deal for all our clients. One example, we were convinced sensor technology and hardware technology were becoming increasingly commoditized. And that sensor tech in particular was going to show up in retail, we thought retail was going to become a technology driven customer experience platform. Rather than just putting that in decks, we started to make stuff, completely proactively. We started to make experience-prototypes in our basement. And then we would essentially go toss that around with other people in the company with related clients. It went from being a group of brains that were working in response to internal questions, to being slightly on the front foot.

SG: When you left, you then went on to create your consultancy Pragmatic Futurism. You went from this indestructible force in this incredibly nice building, and all the things that come with nice buildings, to shooting yourself out of the cannon, so to speak. What was your idea there and what are you trying to accomplish with your consultancy?

NA: It’s funny, Pragmatic Futurism is best described by the things I wasn’t trying to do, rather than what I was. I wasn’t trying to build an agency, and I’m still not. I wasn’t trying to have a payroll that would suck me into doing business development all day long, and I haven’t. I’ve avoided those things. I had an 18-month-old at the time, my wife and I knew we wanted a second, and I was just traveling too much.

To be totally candid, it’s a tiring mission. Change management takes its toll. I was not at my best, I did run out of energy at W+K. I’d lost sight of what real progress looked like. That’s one of the most dangerous things about change management — if you don’t have a clear end point of when you can stop being in those high tension, high stress moments. Or if you never give yourself a moment to lean back and go, okay, we did it — we made some change. Because change is infinite. I just got sucked into wanting more, more, more and the tension got higher.

Pragmatic Futurism was an experiment to see how far I could go with strategic advisory work in this space that I’m so passionate about — brands, humans, and technology. But without having to build this really challenging economic model that is about price arbitrage between a W2 payroll and what I can convince clients that I’ll be working on (but in reality I wouldn’t be). I didn’t want to get sucked into that model. It’s such a tough act: to bridge the gap between project fees on one side, versus your payroll. I knew I didn’t want to do that. I was exhausted from trying to prove the economic viability of that. So I made some choices around the kind of work I was going to do and making clients clear and excited about the expectations. It’s been a ride.

SG: Out of that, and maybe out of COVID and all the things happening in the world, you’ve created this entire product that organizations can subscribe to called OK Tomorrow. What is OK Tomorrow and why does it exist now?

NA: OK Tomorrow is a live show that brings creative and emerging technology based inspiration content to the enterprise. It is a subscription to a highly potent channel of inspiration and learning built specifically for ambitious brand, product, and innovation organizations. Teams that subscribe to OK Tomorrow get access to their own live streamed show, content, and discussions on a regular biweekly basis.

Imagine the best keynote speaker — but turned into a regular cadence every two weeks, and delivered in a way that is super easy to consume for organizations. We’ve built it into a platform that we can “switch on” for any team overnight. Instant inspiration + mind expansion!

The backstory of how I arrived at OK Tomorrow is that I noticed that in strategic advisory assignments, the first 20 or 30% of the assignment, whether it was Reddit, McDonald’s, or Nike as my client, the first 30% of the engagement was very similar: paint a true and inspiring landscape of the amazing and optimistic developments in emerging tech and emerging science, relevant to a business audience. It is really high value — it was me coming in full of perspective, bright eyed and bushy tailed, full of real-world perspective. I come in really well read. I read and I study probably more than anyone else I know in the professional world, because I don’t have any of those other problems. And, I’m free from the politics of corporations.

I’m able to bring an immediate deep perspective on some really important technology stacks. For example, what is crypto tech going to do to everything? How is genetics going to become the next computer platform? What is the world going to be like when we move from constraining energy usage into having infinite energy usage? These are the amazing opportunity areas and existential threats across all commercial enterprises. I’d come in with those and say, I know you asked me a question about the future of sport, but I can’t answer the future of sport until I share all this with you. I have to get this off my chest. The engagement from the clients in return was like, “Wow, I’m learning so much from this perspective.”

SG: It’s learning, which leads to thinking, which leads to creativity.

NA: Exactly. I can’t beat the likes of Accenture and ad agencies at their own game. I can’t beat them with a team of client services people and fancy gift baskets. But I can beat them with the immediacy and the potency of my thinking. I can offer value with straight up intensity. Not that my quest is to beat the competition, but it’s to offer a really immediately high value, strategic advisory product without having to go through six weeks of stakeholder interviews and regurgitate the client’s brief over and over. I got this feedback again and again that what I was doing was really eye opening. The fact that you’re able to take us into different places before you move us into our place.

At the time it was just me, no staff. But I started to wonder if I can turn this into a media company? Should I build the HBO for the enterprise? All we’ve learned in the last 20 years is that the real knife fight is in great storytelling and content creation. The reason TV advertising is on the decline is because TikTok is more fun to watch. That’s the competition. People don’t compartmentalize ads versus content, whatever labels we give as an industry. This is humanity’s desire to be around the campfire and tell stories.

I did a scrub, I looked around, and was like damn, this space is so ripe for disruption. Existing training content — lord. I mean, this is like ’90s stuff, right? This is the stuff you get invited to and you’re like, oh, I have to go to one of these horrible training seminars. So I essentially spliced in the DNA of YouTube streamers, TikTok content creators, John Oliver, that Late Night Show type flavor. I’m focused on what I know, which is where is the puck going and where is emerging technology, emerging science, innovation, creative psychology and physiology taking the entire commercial opportunity? How can you use creativity to change the future of the world’s biggest brands?

SG: What are the shifts that have happened in the world over the last five years that have made us ready for things like this? Obviously COVID has had a lot to do with this, but we have more distributed employees and there’s a greater emphasis on training, upscaling, and retaining employees. It’s become abundantly clear that this ‘90s-style internal training stuff doesn’t work anymore.

NA: There’s no doubt that the Zoom-ification of knowledge work was one, the rise of knowledge work is the other. Whether it’s software automated or not, the automation of labor in general is putting more of an emphasis on IP creation and knowledge work. The final, big validator of this, is that I think we’re moving back to a phase where the generalists will be more appreciated than large teams of specialists. Part of that is a capital markets thing, maybe this milk and honey era of giant tech companies is starting to come down. There is now a quest for efficiency and speed.

So what does that mean? In the marketplace, it’s the agility of the individual, the ability to look at a space and educate yourself about it. And there are now increasingly accepted patterns for absorbing this kind of content in ways that are really easy. That’s what COVID did. The show that we broadcast with OK Tomorrow, it’s a live show, but we record it. Half the people watch it live and half the people watch it audio only on their drive home, they watch it on the Peloton at night. And it’s this agility that really creates this amazing feedback loop. The world was ready for this.

This is a thing that’s been building over time. It’s a bit like change management. We knew it was coming, but I don’t think any of us have acknowledged that we’re there. The internet, really more than anything, was about creating a global library of anything that you ever wanted to know. We knew it was going to be that. Well today you can go and watch a three hour video that Ray Dalio, world famous economist, has created on the macro debt cycle. It’s three hours long. If you were to sit and watch that from beginning to end, you would go from wherever you are in the standard distribution to probably the top 0.1% in the world, most knowledgeable people about the macro debt cycle.

That is the power of the internet. You can move yourself from being a casual observer, to an educated commenter, to a valuable participant in the conversation, in three hours. Now it’s just a choice, are you able to dedicate your mental energy to do that?

SG: What technology has you psyched right now? If you were thinking about creative technology in 2022–23, what are the things that you really want to tie your boat to?

NA: AI and machine learning have been in deep incubation for 15 or 20 years, funded by some of the most wealthy companies, with a tremendous amount of cash flow from Google, Facebook, etc. It was slowly built, but a tremendous amount of cash has gone into that. And there’s been an explosion this year.

For example, we’ve got GPT-3, an algorithm created by OpenAI. It’s a remarkable breakthrough in text generation, in a machine’s ability to bridge the gap between the uncanny valley of human writers and machine based writers. That was a year or two ago, and it was really a moment. And just a couple months ago, we’ve got DALL-E, which was produced by the same team OpenAI. We’ll look back in 10 or 15 years and look at DALL-E as an absolute turning point. Going back to your first question, humans, brands, and technology — the relationship between those is getting tighter and tighter to where I don’t think they’re going to be different. With DALL-E, we essentially have an algorithm that’s reverse engineered how we visually dream. We’ve reverse engineered the unique capability for humans to close our eyes and imagine a scene. Now this machine is able to do that.

Two things are going to happen here. First is, well, what do we do next? Now that we’re able to take that burden off us, what will happen? Then how do you leverage that as a creative person? The immediate kind of media narrative behind this stuff is, “Oh my god, that’s the end of human creativity.” That has been proven wrong so many times. This is going to become an incredible opportunity. Something’s happening in machine based creativity.

Some of the other stuff I’m really into, is the space between our physiology and our creativity. We have these jobs that are about really honing in on the creative product and figuring out what is the original thought? And which original thought is better than the previous one? And that gap is everything. And yet, even with Zoom, we’re still on these nine to five schedules — working Monday to Friday, eating the way we used to, trying to squeeze in a workout before my 9:00 AM meeting. I’m really interested in biotechnologies and nootropics. Caffeine has been the world’s most popular nootropic. A brain altering substance that helps you be more creative and focused, but what’s the next one? There’s lots of interesting work happening in that space. That completely enigmatic mix of sleep, rest, nutrition. All of that stuff is fascinating to me.

And obviously crypto-tech and particularly community centered crypto-tech for the creative space, is fascinating. I went out on my own and I’m having the time of my life. And the bar is still too high for people to do that. A lot of really smart people just get stuck in doing day rate freelancing and it’s a waste. It’s a wasteful way to price your brain and your thoughts. There’s huge opportunities to just change the way that you engage with multiple communities, like Mixing Board. These types of communities are going to get put onto tech platforms that go far beyond Slack and email.


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